Valentines Day Date Night Fashion: What to Wear & What NOT to Wear

GingerSnaps Valentines Day OOTD 1

With Valentines Day around the corner, there has been a lot of talk around the blogosphere this week discussing “the perfect date outfit”.  One article in particular, by Glamour Magazine, suggested “8 Styles to Never Wear on Valentines Day”.  I always find articles like this absurd (no hate, Glamour), so I decided to share with you how I suggest you break (almost) every rule on their list.  You can catch the full article on Glamour Magazines website HERE.

Following my retorts, I have included several examples of Valentines Day OOTD inspiration that break one or more of these silly rules.


Glamour says: “Ok, hear us out on this one. We’re in full support of a Netflix and chill evening, especially on Valentine’s Day. A bottle of wine, Game of Thrones marathon. You got it. Just turn it up a little on February 14 and please—at least opt for the silk pajama pants over college sorority sweatpants.”

Ginger says: This one is the only suggestion I will (reluctantly) agree with, mainly because I have a SEVERE sweat pant addiction that I am actively trying to overcome.  You wouldn’t believe it from my style on the blog, but I am very bipolar when it comes to what I wear.  Only my closest friends know that 99% of the time I am in over-sized, unattractive sweatpants and a mismatched turtleneck.  On fancy days I might opt for Lululemon.  This is not something I am proud of and I totally endorse Glamour on this one, especially for Valentines Day with your sweetie.  UP THE ANTE, ladies!  Maybe even wear those dreadful thigh highs– all men love them and all legs look better in them.  If you have a lot of time on your hands, strap those thigh-highs with a garter belt.  I am convinced garter belts were invented by a man; they take an hour to put on but only five seconds to take off.


Glamour says: “Going home with that special someone after your candle lit dinner? Try to shy away from underwear that needs a team of people to strip off of your body.”

Ginger says: I DO AGREE that you should never let things get hot and heavy while you still have your Spanx on.  However, I encourage you to wear the Spanx if it helps you look your best, just be sure to excuse yourself to the washroom when you arrive at his place to both freshen up AND remove your shape wear.  Problem solved.

Strappy, complicated lingerie.

Glamour says: “Change into that sexy boudoir look after dinner. There is no such thing as a lace-up corset or bow-clad undergarment that doesn’t bunch under your date night look.”

Ginger says: I say, save the complicated lingerie all together, especially if it’s a first date.  The complicated lingerie (i.e. garter belts) take forever to put on, and it will make the mood awkward and could even appear like you’re trying too hard if you take an hour in the bathroom getting “ready” when you’re first getting to know a guy.  If you feel you must wear it, put it on ahead of time and just be sure to wear a dress with a full skirt that has ample length to cover the garters when you sit.

Too-high heels.

Glamour says: “We promise: Heels that you can’t walk in? They don’t look good on anyone.”

Ginger says: This has nothing to do with Valentines Day, this is EVERY DAY!  You look absolutely ridiculous when you wear a pair of heels that you cannot comfortably walk in.  Those heels with the super stacked platforms on the front are not only passé, they are virtually impossible to walk in without clunk-ing about like an amateur stilt-walker.  Even if you are vertically challenged, trust me, you look ridiculous when you teeter around unable to take a normal-sized step.  This actually draws MORE ATTENTION to the fact that you are short and trying to compensate.  If a guy has an issue with height, he probably isn’t going to date you to begin with.  So, stop taking away from your beauty with shoes high than Lady Gaga and concentrate on your sexiest strut instead.

A totally sheer top. 

Glamour says: “While a cutout or eyelet top may reveal a bit of your sexy lace bra, there’s no need to go too bare. Make sure your underwear isn’t totally visible to everyone who looks your way.”

Ginger says: Sheer tops are awesome and a totally sexy option for Valentines Day, as long as you keep the rest of the outfit demure and lady like.  I’m not sure what planet Glamour Magazine is on, but who EVER goes out of the house in a totally sheer top without a bra?  Oh wait, actually I did for THIS recent post where I dressed like “Sexy Little Bo Peep”.   Lesson here is NOT to push the envelope too far, such as wearing a totally sheer top without a bra, when on a date.  Keep those fashion choices for when you’re at an event making a fashion statement, like I do.

Too-tight dresses. 

Glamour says: “As hot as you think you look standing up, have you ever tried to sit down in one of these? Cross your legs? Make this night about you—avoid dresses that force you to think more about how uncomfortable you are than the person sitting across the table from you at dinner.”

Ginger says: The rules for wearing a sexy, tight bodycon dress are 1) always wear the proper shape wear underneath and 2) always cinch your midsection with a large, high-waisted belt.  Follow the rules listed above on shape wear and you’re good to go in a sexy, figure-hugging dress.

Head-to-toe red. 

Glamour says: “We know, red is the color of the holiday. Don a flirty cherry colored mini, a ruby toned lace top, even fire engine hued flats. Just please don’t wear them all together. That, dear friends, is what we like to call over-the-top.”

Ginger says: Of course you can wear head-to-toe monochromatic red!  Just do it in an interesting, fashion-forward way.  I have covered how to wear this trend in detail in THIS post about Monochromatic Red.  In short, just be sure to wear lots of different layers, textures, and shades of red, so you don’t look like you’re match-y match-y.  Additionally, you should never be afraid to be a little over-the-top; that’s how you stand out and make your Valentine only able to concentrate on YOU.

Too much perfume. 

Glamour says: “Make an entrance all on your own. There’s no need for your guy (or gaggle of girls!) to smell you miles before you walk through the door. We don’t care how good that perfume smells after a few puffs.”

Ginger says: I love perfume and of course, don’t overdo it in a soak-myself-with-half-the-bottle kind of way.  However, don’t under do it either.  I love my perfume of choice, Chanel Chance, and I am not only religious about spraying it on my neck, wrists, and hair every day, I also ALWAYS bring it in my purse on a night out and refresh with a quick spritz throughout the night.

GingerSnaps Valentines Day OOTD 1

GingerSnaps Valentines Day Sheer Top OOTD  3

GingerSnaps Valentines Day Monochrome Red 1

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GingerSnaps Sheer Lady Like OOTD 1

GingerSnaps Red and Green TBT OOTD 7

GingerSnaps Valentines Day Tight Dress 1

GingerSnaps Valentines Day Monochrome Red 6

GingerSnaps Sheer Lady Like OOTD 2


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GingerSnaps Valentines Day Bodycon OOTD

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